A method of controlling the growth of bacteria and fungi using the phenylhydrazine salt of 2-mercaptopyridine-n-oxide

ABSTRACT

The phenylhydrazine salt of 2-mercaptopyridine-N-oxide is a novel composition of matter and is useful as a broad spectrum anti-bacterial and anti-fungal agent, especially against Gramnegative organisms.

United States Patent Haugwitz et al.

[54] METHOD OF CONTROLLING THE GROWTH OF BACTERIA AND FUNGI USING THEPI-IENYLI-IYDRAZINE SALT OF Z-MERCAPTOPYRIDINE-N- OXIDE r [72 Inventors:Rudiger D. Haugwitz, Highland Park, N.J.; John Uhoch, Jr., Seymour,Conn.

[52] us. Cl .Q ..424/263 [I51 3,694,553 Sept. 26, 1972 [51] Int. Cl...A0ln 9/00, AOln 9/22 [58] Field of Search ..424/263 [56] ReferencesCited UNITED STATES PATENTS 6/1970 I-laugwitz ..260/294.8G 6/1970Haugwitz ..260/294.8G

Primary Examiner-Albert T. Meyers Assistant Examiner-Allen J. RobinsonAttorney-Gordon D. Byrkit et al.

[57] ABSTRACT The phenylhydrazine salt of Z-mercaptopyridine-N- oxide isa novel composition of matter and is useful as a broad spectrumanti-bacterial and anti-fungal agent, especially against Gram-negativeorganisms.

1 Claim, No Drawings METHOD OF CONTROLLING THE GROWTH OF BACTERIA ANDFUNGI USING THE PHENYLHYDRAZINE SALT OF 2- MERCAPTOPYRIDINE-N-OXIDE Thisis a division of co-pending application Ser. No. 5,914 filed Jan. 26,1970, now U.S. Pat. No. 3,634,438, 1-11-72.

Thisinvention relates to the novel phenylhydrazine salt of2-mercaptopyridine-N-oxide and to the method of controlling the growthof micro-organisms using this salt.

The salt of this invention is prepared by reacting substantiallyequimolar proportions of the reactants suitably dissolved in an aproticinert reaction medium at temperatures from room temperature to 140 C. Oncooling, the product crystallizes and is filtered or otherwise separatedfrom the reaction medium. It is useful as separated or it is suitablyrecrystallized when greater purity is desired.

Suitable inert reaction media include, for example, benzene, toluene,xylenes, petroleum ether, cyclohexane, chloroform, carbon tetrachlorideand tetrachloroethylene.

The reaction time is not critical and may vary from a few minutes tohours or more. Usually from 0.1 to 5 hours is satisfactory.

The compound is useful as a chemotherapeutic agent and is suitablyformulated in any suitable compositions in suitable proportions, asdecongestant, ear drops, foot powders or troches as described in U.S.Pat. No. 2,713,049 at column 3, lines 22-62 or U.S. Pat. No. 2,742,393from column 2, line 35 to column 3, line 10.

EXAMPLE I To a solution of 2.5 g. (0.0,197 mole) ofZ-mercaptopyridine-N-oxide in 20 m1. of benzene was added a solution of2.2 g. (0.022 mole) of phenylhydrazine in 5 ml. of benzene. Theresulting precipitate was filtered off to yield 4.8 g. of initialproduct. Repeated crystallizations from ether furnished the analyticallypure phenylhydrazine salt of 2-mercaptopyridine-N-oxide having a meltingpoint of 72-74 C. with decomposition.

Calc. for C I-1 N 08: C, 56.15; H, 5.57; N, 17.86

percent 2 Found: C, 56.22, 56.36; H, 5.75, 5.84; N, 17.82,

17.53 percent The broad spectrum of anti-bacterial and antifungalactivity of the compound of this invention is shown in Table I andcompared with several widely used commercial products. The advantage ofthe compound of this invention is clearly shown in Table l by its lowminimum inhibitory concentration, especially against Gram-negativeorganisms.

TABLEI Organism Organism No. 1 2 3 4 5 6 Gram ProductofExamplel 1.5 4.53.0 4.5 15 18.0 t-Butyl Ammonium Salt(a) 1.5 4.5 18.0 Ammonium Salt (a)1.5 3.0 12.0 6.0 Acid(a) 1.5 3.012.0 12.0 SodiumSa1t(a) 1.5 3.0 9.0 12.04.5 12.0 HydrazineSalt (a) 3.0 18.0 25.0 6.0 25.0 18.0 CommercialProducts N-(B-Chloroallyl) hexaminiurn chloride 18.7 37.5 75.0 37.5 50.03,4,5-Tribromosalicyl anilide 0.35 0.92 12,5 37.5 A mixture of 3,4',5-

tribromosalicylanilide and 12-20 percent 3,5

dibromosalicylanilide 0.78 4.6 75.0 18.7 50.0 Sodium orthophenylphenate100 100100 100100 Pentachlorophenol,

sodium salt 0.87 3.0 75 75 100 (a) Of Z-mercaptopyridine-N-oxideOrganisms: I Staphylococcus aureus 209 P (2) Streptococcus faecalis SC164 (3) Pseudomonas aeruginosa SC 3840 (4) Proteus vulgaris SC 3855 (5)Aerobacter aerogenes SC 1678 (6) Lactobacillus casei What is claimed is:

l. A method of controlling the growth of bacteria and fungi by applyingto said micro-organisms an effective anti-bacterial and anti-fungalamount of the phenylhydrazine salt of 2-mercaptopyridineN-oxide.

